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Top 10 Best Hawaii Sailing Trips

Found 107 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Happy Hour Sunset Sail on Maui's Luxury Catamaran

(4.8 of 100 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More

Free Cancellation
Start From $169.00
 
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Happy Hour Sunset Sail on Maui's Luxury Catamaran

  • Hawaii
  • Superb100 reviews4.8

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $169.00
 
 

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

(4.9 of 40 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Start From $203.16
 
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

  • Hawaii
  • Superb40 reviews4.9

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Start From $203.16
 
 

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

(4.9 of 137 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $269.00
 
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

  • Hawaii
  • Superb137 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $269.00
 
 

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

(4.9 of 584 reviews)

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red Hill Area lava arches — underwater volcanic terrain, weather per... More

Free Cancellation
Start From $178.72
 
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay

  • Hawaii
  • Superb584 reviews4.9

• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 â....

    Free Cancellation
    Start From $178.72
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 421 reviews)

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More

Free Cancellation
Start From $159.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb421 reviews4.7

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....

    Free Cancellation
    Start From $159.00
 
 

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

(4.8 of 61 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $249.00
 
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

  • Hawaii
  • Superb61 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $249.00
 
 

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

(4.7 of 2,136 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $169.95
 
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed

  • Hawaii
  • Superb2,136 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $169.95
 
 

Kona Morning Snorkel to Captain Cook Monument

(4.9 of 484 reviews)

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump ... More

Free Cancellation
Start From $178.72
 
Kona Morning Snorkel to Captain Cook Monument

Kona Morning Snorkel to Captain Cook Monument

  • Hawaii
  • Superb484 reviews4.9

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leavi....

    Free Cancellation
    Start From $178.72
 
 
-15% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 374 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Start From $84.15
(Saving 15% ) $99.00
 
-15% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb374 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Start From $84.15
    (Saving 15% ) $99.00
 
 
-inf% Nāpali Sunset Dinner Sail

Nāpali Sunset Dinner Sail

(4.7 of 609 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Special Offer
Free Cancellation
Start From $263.82
(Saving inf% ) $0.00
 
-inf% Nāpali Sunset Dinner Sail

Nāpali Sunset Dinner Sail

  • Hawaii
  • Superb609 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Special Offer
    Free Cancellation
    Start From $263.82
    (Saving inf% ) $0.00
 
 
-inf% Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(4.9 of 137 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Special Offer
Free Cancellation
Start From $192.98
(Saving inf% ) $0.00
 
-inf% Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • Hawaii
  • Superb137 reviews4.9

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Special Offer
    Free Cancellation
    Start From $192.98
    (Saving inf% ) $0.00
 
 
-15% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 220 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Special Offer
Free Cancellation
Start From $67.15
(Saving 15% ) $79.00
 
-15% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb220 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Special Offer
    Free Cancellation
    Start From $67.15
    (Saving 15% ) $79.00
 
 
-inf% Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

(4.8 of 761 reviews)

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner Richard Kersten pioneered the large-vessel manta ray snorkel format • Named resident manta... More

Special Offer
Free Cancellation
Start From $141.03
(Saving inf% ) $0.00
 
-inf% Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

Kona Manta Ray Night Snorkel — 85–95% Sighting Rate

  • Hawaii
  • Superb761 reviews4.8

• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mant....

    Special Offer
    Free Cancellation
    Start From $141.03
    (Saving inf% ) $0.00
 
 
-inf% Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

(4.9 of 89 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Special Offer
Free Cancellation
Start From $139.00
(Saving inf% ) $0.00
 
-inf% Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

  • Hawaii
  • Superb89 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Special Offer
    Free Cancellation
    Start From $139.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 64 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Special Offer
Free Cancellation
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • Hawaii
  • Superb64 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Start From $90.01
    (Saving inf% ) $0.00
 
 
-inf% Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

(4.9 of 741 reviews)

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain Cook Monument at Kealakekua Bay, a Marine Life Conservation District on the Kona Coas... More

Special Offer
Free Cancellation
Start From $135.64
(Saving inf% ) $0.00
 
-inf% Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay

  • Hawaii
  • Superb741 reviews4.9

Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catama....

    Special Offer
    Free Cancellation
    Start From $135.64
    (Saving inf% ) $0.00
 
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 326 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Special Offer
Free Cancellation
Start From $72.96
(Saving inf% ) $0.00
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb326 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Special Offer
    Free Cancellation
    Start From $72.96
    (Saving inf% ) $0.00
 
 
-inf% Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Special Offer
Free Cancellation
Start From $53.31
(Saving inf% ) $0.00
 
-inf% Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

  • Hawaii
  • Superb1,335 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Special Offer
    Free Cancellation
    Start From $53.31
    (Saving inf% ) $0.00
 
 
-inf% 3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(4.6 of 1,335 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Special Offer
Free Cancellation
Private Tour
Start From $1,995.00
(Saving inf% ) $0.00
 
-inf% 3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb1,335 reviews4.6

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,995.00
    (Saving inf% ) $0.00
 
 
-inf% Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

(4.8 of 223 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Special Offer
Free Cancellation
Private Tour
Start From $220.54
(Saving inf% ) $0.00
 
-inf% Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch

  • Hawaii
  • Superb223 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $220.54
    (Saving inf% ) $0.00
 
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